HCID 21904340, compound → HCID 86600014, compound

HRID 393353Notes

Reaction equation

HRID 393353 reaction equation
[C:1](=C1N=CC=N1)=[S:2].[NH2:8][CH2:9][CH:10]1[CH2:14][N:13]([C@@H:15]([CH2:19][CH3:20])[C:16]([NH2:18])=[O:17])[C:12](=[O:21])[CH2:11]1>CN(C=O)C>[N:8]([CH2:9][CH:10]1[CH2:14][N:13]([C@@H:15]([CH2:19][CH3:20])[C:16]([NH2:18])=[O:17])[C:12](=[O:21])[CH2:11]1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 21904340HCID 21904340, compoundHCID 60105813HCID 60105813, compound

Product 1

HCID 86600014HCID 86600014, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 100 ml 3 necked flask, fitted with magnetic stirrer and reflux condenser under inert atmosphere, 4.5 g (22.7 mmoles, 1 eq) of thiocarbonylimidazole are dissolved in 25 ml of DMF and the mixture cooled down to 0° C. 4.53 g (22.7 mmoles, 1 eq) of (2S)-2-[4-(aminomethyl)-2-oxo-1-pyrrolidinyl]butanamide 412 in 25 ml of DMF are added dropwise over 30 min, the mixture is stirred 3 hours at room temperature and left overnight. The mixture is concentrated to dryness, the residue is dissolved in 20 ml of toluene, concentrated again to dryness, and the residue is purified by Prep LC (350 g SiO2 CH2Cl2/MeOH/NH4OH, 93.4:6:0.6) to give 3.1 g of crude 49. It is triturated in 20 ml of ether, filtered and the residue (1.9 g) crystallised from 15 ml of acetonitrile to give 1.2 g of pure 49 (22%).

Workup

  1. waitleft overnight
  2. concentrationThe mixture is concentrated to dryness
  3. dissolutionthe residue is dissolved in 20 ml of toluene
  4. concentrationconcentrated again to dryness
  5. customthe residue is purified by Prep LC (350 g SiO2 CH2Cl2/MeOH/NH4OH, 93.4:6:0.6)
  6. customto give 3.1 g of crude 49
  7. customIt is triturated in 20 ml of ether
  8. filtrationfiltered
  9. customthe residue (1.9 g) crystallised from 15 ml of acetonitrile

Sources & evidence

ORD record
ord-20c806884d584c2e80c6647d3a89948c
Source dataset
uspto-grants-2004_10
Patent number
US06806287B2

Reaction notes

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